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$234+ Cheap flights from Midland (MAF) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — SJU
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheap flight deals from Midland to Caribbean

Keep the following information in mind while searching for Midland to Caribbean flight deals. Data was last updated August 18, 2025.

Round-trip from

$297
(American Airlines)

One-way from

$234
(Delta)

Popular in

December

Cheapest in

April

Average price

$565
From Midland Intl to Caribbean
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One-way flight from Midland Intl to Caribbean
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Highest demand for flights based on searches. 7% potential increase in price ($51 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Midland to Caribbean

Cheapest flights from Midland to Caribbean
Explore the most affordable flight options available from Midland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2025.

This American Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/86:01 amMAF - SJU
2 stops16h 36mAmerican Airlines
Mon 9/226:10 amSJU - MAF
2 stops17h 54mAmerican Airlines
Deal found 8/16$297
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/123:35 pmMAF - SJU
2 stops8h 15mSouthwest
Tue 10/215:05 amSJU - MAF
2 stops9h 10mSouthwest
Deal found 8/17$441
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/128:21 pmMAF - SJU
1 stop16h 59mAmerican Airlines
Tue 10/217:00 amSJU - MAF
2 stops13h 10mAmerican Airlines
Deal found 8/17$445
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/112:05 pmMAF - SJU
1 stop7h 33mUnited Airlines
Thu 9/41:05 amSJU - MAF
2 stops13h 57mUnited Airlines
Deal found 8/17$485
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/812:05 pmMAF - SJU
1 stop7h 33mUnited Airlines
Sun 9/211:05 amSJU - MAF
2 stops23h 25mUnited Airlines
Deal found 8/17$507
This American Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/295:00 amMAF - SJU
2 stops12h 25mAmerican Airlines
Sun 11/25:44 amSJU - MAF
1 stop9h 20mAmerican Airlines
Deal found 8/16$561
This American Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/25:00 amMAF - SJU
1 stop8h 25mAmerican Airlines
Sat 9/612:01 pmSJU - MAF
2 stops12h 03mAmerican Airlines
Deal found 8/16$564
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/29:46 amMAF - SJU
2 stops13h 11mUnited Airlines
Fri 9/51:05 amSJU - MAF
2 stops13h 57mUnited Airlines
Deal found 8/17$575
This American Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/208:32 pmMAF - SDQ
2 stops17h 08mAmerican Airlines
Sat 1/104:20 pmSDQ - MAF
2 stops18h 15mAmerican Airlines
Deal found 8/18$1,074

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midland to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 18, 2025.
Use the filters below to find and compare flights from Midland to Caribbean that are best for you.

Fly from

Midland

Fly to

Caribbean

Route

Depart

Return

Price

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 9/8

6:01 am-11:37 pm

2 stops16h 36m

San Juan Luis Munoz Marin Intl

Mon 9/22

6:10 am-11:04 pm

2 stops17h 54m

$297

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Sun 10/12

3:35 pm-12:50 am

2 stops8h 15m

San Juan Luis Munoz Marin Intl

Tue 10/21

5:05 am-1:15 pm

2 stops9h 10m

$441

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Sun 10/12

8:21 pm-2:20 pm

1 stop16h 59m

San Juan Luis Munoz Marin Intl

Tue 10/21

3:34 pm-8:51 am

1 stop18h 17m

$445

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 9/1

12:05 pm-8:38 pm

1 stop7h 33m

San Juan Luis Munoz Marin Intl

Thu 9/4

1:05 am-2:02 pm

2 stops13h 57m

$485

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Wed 10/29

10:45 am-11:50 pm

2 stops12h 05m

San Juan Luis Munoz Marin Intl

Sun 11/2

5:40 am-4:30 pm

2 stops12h 50m

$485

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 9/1

6:01 am-4:05 pm

2 stops9h 04m

San Juan Luis Munoz Marin Intl

Fri 9/5

3:05 pm-10:12 pm

1 stop8h 07m

$485

MidlandSanto Domingo

MAF - SDQ

MAFSDQ

Midland Intl

Sat 12/20

8:32 pm-3:40 pm

2 stops17h 08m

Santo Domingo Las Americas

Sat 1/10

4:20 pm-8:35 am

2 stops18h 15m

$1,074

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Mon 9/15

5:30 am-3:34 pm

2 stops10h 04m

$234

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Mon 9/15

5:00 am-2:05 pm

1 stop9h 05m

$234

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Thu 12/25

5:25 am-7:50 pm

2 stops12h 25m

$347

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 12 results
1
2

Best time to book a flight from Midland to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Midland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Midland to Caribbean

What is the cheapest month to book a flight from Midland to Caribbean?

Currently, September is the cheapest month in which you can book a flight from Midland to Caribbean (average of $254). Flying from Midland to Caribbean in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MAF to CB?

Find hourly flight availability from Midland to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 18, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Midland to Caribbean as you normally would.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated August 18, 2025.
Read through reviews of airlines operating flights from Midland to Caribbean, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,925 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Midland to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Midland to Caribbean?

    Most people fly from Midland Intl (MAF) if they book a flight from Midland to Caribbean. Midland Intl is conveniently located just 8.2 mi from Midland’s city center.

  • How long is the flight from Midland to Caribbean?

    Airlines like American Airlines and Southwest fly from Midland to Caribbean in about 8h 15m. The time it takes to get you to your destination can typically vary by up to 8h 21m. The distance from Midland to Caribbean is about 2432 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Midland to Caribbean one-way?

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $234. However, be on the lookout for offers from American Airlines and United Airlines, as they are both options that can get you from Midland to Caribbean for a low price.

  • What are the most popular routes from Midland to Caribbean?

    The most popular flight routes from Midland to Caribbean are Midland Intl - San Juan Luis Munoz Marin Intl, Midland Intl - Santo Domingo Las Americas and Midland Intl - Santa Clara.

  • Can I find deals for flights from Midland to Caribbean that include hotel bookings?

    Yes. In addition to deals on Midland to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midland to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midland to Caribbean.

  • Can I find deals for business class flights from Midland to Caribbean?

    Yes. Cheapflights offers flight deals from Midland to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Midland to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Midland to Caribbean (average of $254). Flying from Midland to Caribbean in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 3 airlines flying from Midland to Caribbean

Discover the top 3 airlines that operate flights from Midland to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$349Average$935FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$370Average$585FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$513Average$544FlexibilityNo cancel feeOn-time63%

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